Enzymatic resolution of 2-dialkylaminomethylcyclopentanols and - cycloheptanols

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Abstract

Extensive lipase screening was performed in relation to the asymmetric acetylation of rac-2-dialkylaminomethylcyclanols 1-5. The lipase PS- and Novozym 435-catalysed resolutions of compounds 1-5 were based on asymmetric acylation of the secondary OH group at the R-stereogenic centre with various vinyl esters, in different organic media. High enantioselectivity (E>200) was observed when vinyl acetate was used as acylating agent, with diethyl ether or with diisopropyl ether as solvent. The reaction rates were markedly affected by the size of the alicyclic ring, and by the solvent.

Original languageEnglish
Pages (from-to)1985-1993
Number of pages9
JournalTetrahedron Asymmetry
Volume10
Issue number10
DOIs
Publication statusPublished - May 21 1999

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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